Oprah Tries 3 Iconic Looks for Her October Cover Shoot
Travel through the '50s, '60s and '70s in style.
![oprah october cover oprah october cover](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-70s-1-949x1356.jpg)
Photo: Sioux Nesi
Simply '70s
The free and easy, hippie-go-lucky vibe of the '70s called for loose, flowing hair and big, soft lashes.
Top, Etro, $3,243; 212-317-9096. Jeans, White House Black Market, $84; WHBM.com. Hat, $255; Sayatwena.com. Earrings, $2,500; JihadleyJewelry.com. Silver ring, $90; Pandora.net. Lapis lazuli and gray tigereye and azurite rings, Heather Benjamin, $450 to $460 each; Neiman Marcus Beverly Hills, 310-550-5900. Bag, Roger Vivier, $2,250; 212-861-5371. Shoes, Nicholas Kirkwood, $795; MatchesFashion.com.
Top, Etro, $3,243; 212-317-9096. Jeans, White House Black Market, $84; WHBM.com. Hat, $255; Sayatwena.com. Earrings, $2,500; JihadleyJewelry.com. Silver ring, $90; Pandora.net. Lapis lazuli and gray tigereye and azurite rings, Heather Benjamin, $450 to $460 each; Neiman Marcus Beverly Hills, 310-550-5900. Bag, Roger Vivier, $2,250; 212-861-5371. Shoes, Nicholas Kirkwood, $795; MatchesFashion.com.
![oprah 70s hair oprah 70s hair](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-70s-3-949x1356.jpg)
Photo: Sioux Nesi
The Hair
"This was my favorite look. For fullness, I added really long extensions. And lots of gold and red highlights helped bring the style up-to-date." —Andre Walker, hairstylist
![oprah 70s wardrobe oprah 70s wardrobe](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-70s-5-949x1356.jpg)
Photo: Sioux Nesi
Our cover girl's selection of colorful '70s-inspired tunics.
![adam glassman hat adam glassman hat](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-70s-4-949x1356.jpg)
Photo: Sioux Nesi
O creative director Adam Glassman gets lost in one of Oprah's hats.
![oprah hat oprah hat](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-70s-7-949x1356.jpg)
Photo: Sioux Nesi
"I have a big head! The only hats that fit me are custom made." —Oprah
![oprah 70s makeup oprah 70s makeup](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-70s-9-949x1356.jpg)
Photo: Sioux Nesi
The Makeup
"To create a wide-eyed effect, I went with very spiky eyeliner. The muted, pale lip is a contrast to the boldness of the eye makeup." —Derrick Rutledge, makeup artist
![oprah 70s lashes oprah 70s lashes](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-70s-8-949x1356.jpg)
Photo: Sioux Nesi
Derrick pieced together Oprah's faux lashes. "They felt like little spiders," she says.
![oprah 60s cover oprah 60s cover](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-60s-1-949x1356.jpg)
Photo: Sioux Nesi
Sweetly '60s
Mod style blended innocence with smooth sophistication: The dress code was snappy, the hair was pert and the lipstick? Pink.
"I love what a hit of color can do for your mood!" —Oprah
Trenchcoat, $2,395; Burberry.com. Sweater, $80; Uniqlo.com. Skirt, $138; JCrew.com. Earrings, Silvia Furmanovich, $8,600; Neiman Marcus Beverly Hills, 310-550-5900. Watch, Apple Watch, $10,000; Apple.com. Ring, Yossi Harari, $5,820; Bergdorf Goodman, 888-774-2424. Bag, $5,300; Fendi.com. Shoes, Bally, $750; 844-44-BALLY for similar styles.
"I love what a hit of color can do for your mood!" —Oprah
Trenchcoat, $2,395; Burberry.com. Sweater, $80; Uniqlo.com. Skirt, $138; JCrew.com. Earrings, Silvia Furmanovich, $8,600; Neiman Marcus Beverly Hills, 310-550-5900. Watch, Apple Watch, $10,000; Apple.com. Ring, Yossi Harari, $5,820; Bergdorf Goodman, 888-774-2424. Bag, $5,300; Fendi.com. Shoes, Bally, $750; 844-44-BALLY for similar styles.
![oprah 60s hair oprah 60s hair](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-60s-4-949x1356.jpg)
Photo: Sioux Nesi
The Hair
"I teased Oprah's hair at the crown but didn't go overboard. If your style feels authentic, you won't look like you're in a costume." —Andre
![oprah 60s inspiration oprah 60s inspiration](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-60s-3-949x1356.jpg)
Photo: Sioux Nesi
One of the inspirations for Oprah's voluminous do? Catherine Deneuve's iconic look in 1967's Belle de Jour.
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Photo: Sioux Nesi
The Makeup
"A rosy mouth is very '60s Mod—and it also happens to be very hot right now. I defined Oprah's eyes by emphasizing her beautiful brows." —Derrick
![pink lipstick oprah pink lipstick oprah](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-60s-5-949x1356.jpg)
Photo: Sioux Nesi
"I would never have tried pink lipstick unless it was for a cover shoot." —Oprah
![oprah pink lipstick oprah pink lipstick](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-60s-7-949x1356.jpg)
Photo: Sioux Nesi
"I'm stepping out of my comfort zone with this shade!" says Oprah. "It's called Pink Sugar."
![oprah 50s cover oprah 50s cover](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-covers-50s-1-949x1356.jpg)
Photo: Sioux Nesi
Fabulous '50s
No one embodies classic '50s chic quite like Audrey Hepburn. It's go-for-broke beauty with dramatically upswept hair, matching lips and nails in candy apple red and heavy-duty eyeliner.
Dress, St. John, $1,395; 212-755-5252. Earrings, Dani by Daniel K, $1,050; Moray's Jewelry, 305-374-0739. Watch, Tiffany & Co., $14,000; Tiffany.com. Bracelet, Chanel Fine Jewelry, $118,000; 800-550-0005. Ring, Mastoloni, $15,400; 800-347-3275. Hairpins, $100 to $115 each; ThomasLaine.com.
Dress, St. John, $1,395; 212-755-5252. Earrings, Dani by Daniel K, $1,050; Moray's Jewelry, 305-374-0739. Watch, Tiffany & Co., $14,000; Tiffany.com. Bracelet, Chanel Fine Jewelry, $118,000; 800-550-0005. Ring, Mastoloni, $15,400; 800-347-3275. Hairpins, $100 to $115 each; ThomasLaine.com.
![](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-50s-2-949x1356.jpg)
Photo: Sioux Nesi
"Trends come and go, but a classic look always feels right." —Oprah
![oprah 50s hair oprah 50s hair](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-50s-3-949x1356.jpg)
Photo: Sioux Nesi
The Hair
"The key to a great updo is to make it look as unstructured and casual as possible. You can see that Oprah's hair is very airy, which is how she likes it. The black ribbon and sparkling combs added just a hint of formality." —Andre
![oprah 50s inspiration oprah 50s inspiration](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-50s-4-949x1356.jpg)
Photo: Sioux Nesi
Chanel's full 2015 runway models were a muse for Oprah's ribbon-and-sparkle combo.
![oprah audrey hepburn oprah audrey hepburn](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-50s-5-949x1356.jpg)
Photo: Sioux Nesi
"Look! It's Audrey Oprah Hepburn." —Oprah
![updo updo](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-50s-6-949x1356.jpg)
Photo: Sioux Nesi
How up was Oprah's updo? Eight inches, Andre estimated.
![oprah 50s makeup oprah 50s makeup](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-50s-6-949x1356.jpg)
Photo: Sioux Nesi
The Makeup
"One of the main features of this look is the cat eye. When you use such prominent liner, you need to balance it by really playing up the lashes as well. Scarlet lips and nails are elegant and striking against the black of Oprah's outfit." —Derrick
![gayle phone gayle phone](/g/image-resizer?width=670&link=https://static.oprah.com/images/o2/201510/201510-omag-cover-50s-8-949x1356.jpg)
Photo: Sioux Nesi
Gayle checks out a mock cover on her phone. "Didn't you dream of being Audrey Hepburn when you were little?" she asked her pal.
From the September 2015 issue of O, The Oprah Magazine